


Coffee Stains and Windowpanes

by HalfwayToHell



Series: American Sweetheart [2]
Category: Supernatural RPF
Genre: Alternate Universe - Student/Teacher, Anal Plug, Anal Sex, Feminization, M/M, Masturbation, Sex Toys, Teacher-Student Relationship, Webcam/Video Chat Sex
Language: English
Status: Completed
Published: 2016-08-23
Updated: 2016-08-23
Packaged: 2018-08-10 04:58:15
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 2,545
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7831186
Author URL: https://archiveofourown.org/users/HalfwayToHell/pseuds/HalfwayToHell
Summary: <blockquote class="userstuff">
              <p>Since meeting the boy over the webcam, Jensen had thought there would never be someone as lovely as him. He finds himself proven wrong on the first day of class when he meets Jared--a sweet, shy, doe-eyed boy in his Literary Analysis class. Jensen--in all of his years of teaching--had never felt the way he did when he looked at Jared. He had never felt the shuddering in his chest cavity and his dark desires whisper to him constantly. They whisper of Jared's loveliness, of how innocent he looks, and of how Jensen must have him. Ever since that moment their eyes met in his classroom, Jensen's thoughts are corrupted with the images of the freshman boy in a baggy sweatshirt and Converse.</p>
            </blockquote>





	Coffee Stains and Windowpanes

**Author's Note:**

> Official American Sweetheart Playlist:
> 
> Stevie Nicks- Has Anyone Ever Written Anything For You  
> Angus & Julia Stone- You’re The One That I Want  
> Cold Specks- Winter Solstice  
> Nicole Dollanganger- Flowers Of Flesh And Blood  
> Noah Gundersen- Slow Dancer  
> Ben Harper and the Innocent Criminals- Goodbye To You  
> Lacey Sturm- Run To You  
> The Lumineers- White Lie  
> Hearts & Colors- Lighthouse (Acoustic version)  
> Shawn Mendes- Mercy  
> The Strumbellas- I Still Make Her Cry  
> The Strumbellas- The Night Will Save Us

                                                           

 

* * *

 

The sounds of shuffling feet could be heard as Jensen leaned against the front of his new desk, his arms folded across his chest and his eyes had drifted closed a few minutes prior. As he waited for all of his students to find their seats, Jensen took the opportunity to rest his eyes for a few moments. Even after multiple cups of coffee—some with an extra shot of espresso—the effects of his lack of sleep still caused his eyes to burn, fatigue’s claws digging into him. Jensen couldn’t say that he regretted the night before, because he didn’t, but he had wished that he took the opportunity to sleep—even if it was a mere four hours.

 

The silence caused his eyes to open and he was greeted with roughly fifty young faces staring at him with expectant gazes. Jensen smiled.

 

"Good morning, everyone," He greeted and in turn received a few greetings back. "Welcome to Literary Analysis. If this is not the class you are searching for, then I am afraid you're in the wrong room. However, for those of you who have found the right place, unfortunately you'll be spending the next semester with me." He paused for a moment and his smile widened when some of his student's returned his bright smile.

 

"My name is Jensen, although for professionalism's sake, you can call me Mr. Ackles. Now before we get into formalities, I'm going to go over the expectations in regards to this course. I will hand out a syllabus to each and every one of you with the same expectations for you to keep, but I have found in my many years of teaching that the majority of students will not read the syllabus on their own--"

 

Jensen broke off suddenly when he heard giggling. His eyes drifted up to the third row, where two dark haired girls—one of them wore her hair up into a high ponytail and the other had her hair down—were whispering and bantering lightheartedly back and forth in the corner, as if they had forgotten where they were or that their actions were seemingly oblivious. Irritation graced his facial features and Jensen reached behind him, plucking up the class list and began to scan through the many names and faces until he found the girls.

 

He cleared his throat loudly, catching the girls' attention and he raised a disapproving eyebrow. "Danneel Harris. Genevieve Cortese." At the mention of their names, blush colored their cheeks and they both sank low in their seats. "If you ladies have something of importance to talk about, you may step out into the hallway or wait until class is over. Which one shall it be?"

 

"Sorry, Mr. Ackles," The girls mumbled in unison, embarrassment painted on their faces.

 

Jensen eyed them one last time for good measure before he continued.

 

“As I was saying,” He resumed, refolding his arms across his chest, his backside still leaning against the edge of his desk. “expectations. One of them being respect for yourself, respect for your fellow classmates, and respect for me,”—At this, Jensen shot the girls another glance— “The second is turning assignments in on time. Unless otherwise arranged with me, I will not accept late work. You’re adults in college now and I expect you all to act as such. And finally, punctuality--”

 

As if on cue, the door to his classroom suddenly burst open and a boy ducked into the classroom. Without even glancing in Jensen’s direction, the boy—with his head down—made a mad dash for the nearest available desk, which unfortunately for him, was right in front of Jensen.

 

Jensen watched with marginal interest as the boy swiftly removed the backpack from his shoulders and sat down. He studied the boy for a moment in complete silence.

 

The boy had shaggy nut brown hair that curled around the tops of his ears and swept across his forehead, the tips falling into eyes that had yet to look up at him. He wore an olive green sweatshirt that was a size too big for him, his slender frame was drowning in the light fabric and the curve of his—what Jensen could only describe as lovely—collarbones could be seen. The boy tapped his black Converse against the linoleum, his leg bouncing rapidly and the boy bit the top of his thumb with one hand while the other fingered the leather cord around his slim throat—a notion Jensen knew to be a nervous tick.

 

A few minutes of silence passed before the boy had dared to look up at Jensen and when he did, Jensen was met—not so surprisingly—with a pair of kaleidoscope eyes and a pretty, youthful face. The boy was baby-faced with soft looking skin and a creamy complexion. His nose was slender and upturned and there was a beauty mark off to the side of his nose. The boy’s eyelashes were long and thick, swaddling the pair of doe eyes that were staring up at Jensen.

 

“ _Punctuality,_ ” He breathed out at last. “is key in this course. As I have stated before—I do understand that life happens and events will take place that is out of our control, but please do keep in touch with me via my office phone number or my email in case of an emergency. Any questions so far?”

 

When none of his students spoke up, Jensen made his way over to the classroom door. “In regards to punctuality, this door will close and lock five minutes after class begins each day,” Jensen paused to demonstrate locking the door and shutting it. “I am not like most professors that you all have met. I will not tolerate any of my students coming into my classroom late. Not only would your presence disrupt myself, but your fellow classmates as well,”—At this, he flicked his gaze in the boy’s direction, who met his gaze straight on— “This is why I have the five-minute grace period in place.”  

 

Jensen made his way back to the front of the classroom, stopping within a few feet of the boy’s desk. He flashed all his students a smile when he noticed all the nervous jittering and equally nervous smiles that were returned.

 

“Now let’s all get acquainted with one another. Each of you will stand and give us your name and something interesting about you. Since I’ve already given you all my name, I will begin first. My interesting fact is that I recently moved down here from Los Angeles after teaching for nearly ten years at UCLA.”   

 

After a few meaningless questions—Why did he take the job here? Does he have any children? Is he married? etc.—Jensen allowed his students to begin the activity. He nodded and smiled politely at each of his students, asking a question or two to engage with them, but he wasn’t truly listening until it got to the boy right in front of him.

 

Calculated—like a colt standing for the first time—the boy rose from his seat, his fingernails digging nervously into the flesh of his palm and he licked anxiously at his bottom lip. The boy took in a deep, bracing breath before he spoke.

 

“Hi. I’m Jared and there’s nothing interesting about me,” He spoke softly, his voice as young and as pretty as his face.

 

“Nothing at all?” pressed Jensen, doubting highly that there was not a single thing interesting about the boy.

 

Jared was silent for a long moment. It felt as though the classroom was on a sudden incline, the gravitational pull from the students behind the boy urging him on in silence.

 

“Nothing that I am comfortable with sharing out loud,” Jared finished at last, sinking back into his seat.

 

Although he was exceptionally disappointed, Jensen allowed it to slip. After the last student had stood and participated in the activity, he began that day’s lesson. It was only a half an hour into class and as Jensen was discussing the different lenses his student would be expected to analyze diverse pieces of literature through each one, he heard soft sound—something like a mix between sighs and breaths.

 

Turning around, Jensen caught sight of Jared sleeping on his desk. His arms were tucked up underneath his small chest and his cheek was resting against the pages of the open book on his desk. Pursing his lips in annoyance, Jensen grabbed the bulky Dictionary off of his desk and walked toward Jared. He didn’t stop until he was mere feet in front of the boy and dropped the book. The Dictionary slammed to the linoleum with the trivial force of a nuclear bomb.

 

Jared came alive with a gasp and shot upward, as if there were strings attached to his spinal column. The boy couldn’t distance himself from Jensen due to the fact that the chair was bolted to the desk, but he had tried, his back rod stiff against the chair. Jensen had startled Jared so badly, that there were actual tears glistening in the thickness of his eyelashes and his bottom lip trembled ever so slightly.

 

Seeing that look on the boy’s face and to know that he was the reasoning behind it, caused an ache to shudder in his chest, but Jensen shoved it down, refusing to feel any sort of guilt for the boy falling asleep in his own classroom.

 

Jensen left the Dictionary in front of Jared’s desk as a reminder while he taught. Throughout the rest of the class period, Jared stayed awake, but he kept his eyes downcast, his lashes creating crescent moon shadows beneath his eyes and Jensen had thought—just for a moment—how divine he looked that way.

 

In all his years of teaching, Jensen had never looked at any of his students the way he looked at Jared. He had thought that some of his students were attractive or pretty even, but the boy in his class was lovelier than any person he had laid his eyes on—except maybe the boy over the webcam and perhaps—if he was being honest with himself—there was a part of him that believed that they were both equally exquisite, in their own way.

 

♥  ♥  ♥  ♥

 

It took the ding from his laptop to pull Jensen from the deep crevices of his thoughts.

 

Since he arrived home, he hadn’t stopped thinking about Jared—thinking about the look on the boy’s face that he had caused, thinking about how he had frightened the boy to almost the point of tears. There was a part of him that was actually _thrilled_ by the glistening of tears in Jared’s eyelashes, there was a darker portion to him—a darker fragment of his desires—that Jensen did not recognize, but that he could not lie and say it was not him or his own thoughts. The most depraved part of his desires wanted to see those tears on Jared’s eyelashes again, except this time, he wanted the tears to be creations of pleasure and not necessarily fear.

 

  * **BUBBLEGUM BITCH:** _Mr. Ross? Is everything alright?_



 

Jensen’s eyes fell on the boy on the webcam. He was wearing a rose-colored lingerie set this time, his slender hand fingering the pearls on the necklace around his neck and his mouth was painted with the same rose shade.

 

  * **ROSS:** _Just distracted is all._



 

The boy flashed a sultry smile, a set of dimples creasing in his cheeks.

 

  * **BUBBLEGUM BITCH:** _Then let me be your distraction._



 

Jensen wasn’t about to object where the boy on the webcam was concerned. He leaned back in his office chair and watched as the boy shimmied out of the rose satin panties, keeping the stockings and the pearl necklace on. Then the boy disappeared from the screen for a moment only to return with a special prize in his hands. Jensen’s breath caught in his chest cavity and he sat up in his chair, his gaze expectant.

 

The boy turned around so that his bare backside was facing the camera. A hiss ripped through his clenched teeth. An anal plug was nestled between the boy’s ass cheeks and for a moment, Jensen thought that maybe the boy had planned this and that thought alone caused his cock to twitch within the confines of his jeans.

 

Slowly, the boy removed the plug to reveal a perfectly worked open hole, shining still with the lube the boy had used when first inserting it. The boy turned back around to face the camera and picked up the toy lying beside him.   

 

He ran his lips along the underside of the pink dildo, swirling his tongue along the head. The boy then picked up the small bottle of lube beside him and squeezed an ideal amount into the palm of his other hand before he stroked the dildo with his lube slicked hand, making sure to thoroughly coat the toy.

 

The boy shifted to the side, straddling the toy. Leisurely, the boy guided the head of the dildo past the worked open entrance of his hole. A gasp came from the boy which was accompanied by a groan as he sank completely down onto the toy. He then removed the pearls from around his neck and twisted them around his wrists until he created make-shift cuffs.

 

The boy leaned forward, bracing his hands against his mattress as he slowly rocked his hips back and forth on the dildo, whimpers falling past his lips. Cock aching, Jensen opened the fly of his jeans and began to stroke himself as he watched the boy fuck himself on the toy. With each swivel of his hips, Jensen wished the boy was riding his cock instead of the pink plastic one, wishing he could feel the tight, slick insides and how the inner muscles would cling onto him.

 

Gradually, the boy started to grind his hips faster and harder, causing the springs in his mattress to creak with the shifting of his weight. Broken moans bubbled out of the boy’s throat and his shoulders were hunched, his fingers digging into the sheets.

 

When the orgasm hit the boy, his back bowed as the violent climax came over him. Jensen’s own orgasm struck him—as usual—a few moments after the boy’s. Panting, he watched as the boy slowly removed the dildo and recomposed himself once more before his laptop dinged.

 

  * **BUBBLEGUM BITCH:** _Is there anything else I can do for you tonight, Mr. Ross?_



 

As always, Jensen replied with his signature response.

 

  * **ROSS:** _I would settle for your name._



 

The same soft smile from the night before graced the boy’s lips and as per usual, the boy answered the same way he did every time.

 

  * **BUBBLEGUM BITCH:** _Goodnight, Mr. Ross._



 

This time after the screen had gone black, Jensen felt empty. Void. He was not sure what caused this difference in him and after a long while of silence staring into the black abyss of the screen, he realized it was because even though the boy on the webcam distracted him for a good ten to fifteen minutes, his thoughts still returned to Jared.

 

And he did not have the slightest inkling as to why.

 

* * *

 


End file.
